Bio-adipic acid production by catalysed hydrogenation of muconic acid in mild operating conditions
[Display omitted] •Muconic to adipic acid hydrogenation on 5% Pt/C.•Mild conditions: 4bar, 50–70°C, 60–90min.•Catalyst is stable and reusable, 100% selective.•Catalyst characterization pre-post reaction.•Insight on industrial bioprocess downstream. In this work trans,trans-muconic acid was hydrogena...
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Veröffentlicht in: | Applied catalysis. B, Environmental Environmental, 2017-12, Vol.218, p.220-229 |
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creator | Capelli, S. Rosengart, A. Villa, A. Citterio, A. Di Michele, A. Bianchi, C.L. Prati, L. Pirola, C. |
description | [Display omitted]
•Muconic to adipic acid hydrogenation on 5% Pt/C.•Mild conditions: 4bar, 50–70°C, 60–90min.•Catalyst is stable and reusable, 100% selective.•Catalyst characterization pre-post reaction.•Insight on industrial bioprocess downstream.
In this work trans,trans-muconic acid was hydrogenated to adipic acid, a strategic intermediate for the industry of polyamides and high performance polymers. This study: (1) develops a new and robust analytical method for the evaluation of muconic acid conversion and adipic acid selectivity, (2) defines a standard procedure for the confirmation of the kinetic regime using experimental data and some practical criteria to exclude mass transfer limitations, (3) tests Pt/C 5% commercial catalyst for the study of muconic acid hydrogenation at different operating conditions, (4) hypothesizes a reaction pathway in aqueous media, and (5) demonstrates the possibility to recycle the catalyst without loss in activity and selectivity. The developed analytical method evaluates muconic acid conversion by UV–vis analyses, while the selectivity towards adipic acid and mono-unsatured intermediates was determined by GC/TCD analysis after derivatization of the reaction mixture. Under optimized conditions the hydrogenation reaction (70°C, 4bar of hydrogen and 10 substrate/catalyst ratio (wt/wt)) reached full conversion with full selectivity toward adipic acid in 2h. Finally, recycling tests revealed the possibility to reuse catalyst up to 10 times without loss in conversion and selectivity opening the way to a scaling up of the process. |
doi_str_mv | 10.1016/j.apcatb.2017.06.060 |
format | Article |
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•Muconic to adipic acid hydrogenation on 5% Pt/C.•Mild conditions: 4bar, 50–70°C, 60–90min.•Catalyst is stable and reusable, 100% selective.•Catalyst characterization pre-post reaction.•Insight on industrial bioprocess downstream.
In this work trans,trans-muconic acid was hydrogenated to adipic acid, a strategic intermediate for the industry of polyamides and high performance polymers. This study: (1) develops a new and robust analytical method for the evaluation of muconic acid conversion and adipic acid selectivity, (2) defines a standard procedure for the confirmation of the kinetic regime using experimental data and some practical criteria to exclude mass transfer limitations, (3) tests Pt/C 5% commercial catalyst for the study of muconic acid hydrogenation at different operating conditions, (4) hypothesizes a reaction pathway in aqueous media, and (5) demonstrates the possibility to recycle the catalyst without loss in activity and selectivity. The developed analytical method evaluates muconic acid conversion by UV–vis analyses, while the selectivity towards adipic acid and mono-unsatured intermediates was determined by GC/TCD analysis after derivatization of the reaction mixture. Under optimized conditions the hydrogenation reaction (70°C, 4bar of hydrogen and 10 substrate/catalyst ratio (wt/wt)) reached full conversion with full selectivity toward adipic acid in 2h. Finally, recycling tests revealed the possibility to reuse catalyst up to 10 times without loss in conversion and selectivity opening the way to a scaling up of the process.</description><identifier>ISSN: 0926-3373</identifier><identifier>EISSN: 1873-3883</identifier><identifier>DOI: 10.1016/j.apcatb.2017.06.060</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Acid production ; Adipic acid ; Bio-adipic acid ; Catalysis ; Catalysts ; Conversion ; Heterogeneous catalysis ; Hydrogen storage ; Hydrogenation ; Intermediates ; Mass transfer ; Muconic acid ; Platinum ; Polyamide resins ; Polyamides ; Polymers ; Scaling ; Selectivity</subject><ispartof>Applied catalysis. B, Environmental, 2017-12, Vol.218, p.220-229</ispartof><rights>2017 Elsevier B.V.</rights><rights>Copyright Elsevier BV Dec 5, 2017</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c371t-e4f7b896a25b4479b3d1fdd42afb090adee8c43cbc74e9cf50e8210a36d9325a3</citedby><cites>FETCH-LOGICAL-c371t-e4f7b896a25b4479b3d1fdd42afb090adee8c43cbc74e9cf50e8210a36d9325a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.apcatb.2017.06.060$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Capelli, S.</creatorcontrib><creatorcontrib>Rosengart, A.</creatorcontrib><creatorcontrib>Villa, A.</creatorcontrib><creatorcontrib>Citterio, A.</creatorcontrib><creatorcontrib>Di Michele, A.</creatorcontrib><creatorcontrib>Bianchi, C.L.</creatorcontrib><creatorcontrib>Prati, L.</creatorcontrib><creatorcontrib>Pirola, C.</creatorcontrib><title>Bio-adipic acid production by catalysed hydrogenation of muconic acid in mild operating conditions</title><title>Applied catalysis. B, Environmental</title><description>[Display omitted]
•Muconic to adipic acid hydrogenation on 5% Pt/C.•Mild conditions: 4bar, 50–70°C, 60–90min.•Catalyst is stable and reusable, 100% selective.•Catalyst characterization pre-post reaction.•Insight on industrial bioprocess downstream.
In this work trans,trans-muconic acid was hydrogenated to adipic acid, a strategic intermediate for the industry of polyamides and high performance polymers. This study: (1) develops a new and robust analytical method for the evaluation of muconic acid conversion and adipic acid selectivity, (2) defines a standard procedure for the confirmation of the kinetic regime using experimental data and some practical criteria to exclude mass transfer limitations, (3) tests Pt/C 5% commercial catalyst for the study of muconic acid hydrogenation at different operating conditions, (4) hypothesizes a reaction pathway in aqueous media, and (5) demonstrates the possibility to recycle the catalyst without loss in activity and selectivity. The developed analytical method evaluates muconic acid conversion by UV–vis analyses, while the selectivity towards adipic acid and mono-unsatured intermediates was determined by GC/TCD analysis after derivatization of the reaction mixture. Under optimized conditions the hydrogenation reaction (70°C, 4bar of hydrogen and 10 substrate/catalyst ratio (wt/wt)) reached full conversion with full selectivity toward adipic acid in 2h. Finally, recycling tests revealed the possibility to reuse catalyst up to 10 times without loss in conversion and selectivity opening the way to a scaling up of the process.</description><subject>Acid production</subject><subject>Adipic acid</subject><subject>Bio-adipic acid</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Conversion</subject><subject>Heterogeneous catalysis</subject><subject>Hydrogen storage</subject><subject>Hydrogenation</subject><subject>Intermediates</subject><subject>Mass transfer</subject><subject>Muconic acid</subject><subject>Platinum</subject><subject>Polyamide resins</subject><subject>Polyamides</subject><subject>Polymers</subject><subject>Scaling</subject><subject>Selectivity</subject><issn>0926-3373</issn><issn>1873-3883</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp9UMtKxDAUDaLgOPoHLgKuW_PqIxtBxRcMuNF1SJPbMWWmqUkr9O_NWN0KB-7iPC7nIHRJSU4JLa-7XA9Gj03OCK1yUiaQI7SidcUzXtf8GK2IZGXGecVP0VmMHSGEcVavUHPnfKatG5zB2jiLh-DtZEbne9zMOKXq3RzB4o_ZBr-FXv9QvsX7yfj-z-V6vHc7i_0AISn6LU6kdQdtPEcnrd5FuPi9a_T--PB2_5xtXp9e7m83meEVHTMQbdXUstSsaISoZMMtba0VTLcNkURbgNoIbhpTCZCmLQjUjBLNSys5KzRfo6slN1X4nCCOqvNT6NNLRaUQRSGlLJNKLCoTfIwBWjUEt9dhVpSow5qqU8ua6rCmImUCSbabxQapwZeDoKJx0BuwLoAZlfXu_4BvHd6BSg</recordid><startdate>20171205</startdate><enddate>20171205</enddate><creator>Capelli, S.</creator><creator>Rosengart, A.</creator><creator>Villa, A.</creator><creator>Citterio, A.</creator><creator>Di Michele, A.</creator><creator>Bianchi, C.L.</creator><creator>Prati, L.</creator><creator>Pirola, C.</creator><general>Elsevier B.V</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>JG9</scope><scope>KR7</scope><scope>L7M</scope><scope>SOI</scope></search><sort><creationdate>20171205</creationdate><title>Bio-adipic acid production by catalysed hydrogenation of muconic acid in mild operating conditions</title><author>Capelli, S. ; Rosengart, A. ; Villa, A. ; Citterio, A. ; Di Michele, A. ; Bianchi, C.L. ; Prati, L. ; Pirola, C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c371t-e4f7b896a25b4479b3d1fdd42afb090adee8c43cbc74e9cf50e8210a36d9325a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acid production</topic><topic>Adipic acid</topic><topic>Bio-adipic acid</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Conversion</topic><topic>Heterogeneous catalysis</topic><topic>Hydrogen storage</topic><topic>Hydrogenation</topic><topic>Intermediates</topic><topic>Mass transfer</topic><topic>Muconic acid</topic><topic>Platinum</topic><topic>Polyamide resins</topic><topic>Polyamides</topic><topic>Polymers</topic><topic>Scaling</topic><topic>Selectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Capelli, S.</creatorcontrib><creatorcontrib>Rosengart, A.</creatorcontrib><creatorcontrib>Villa, A.</creatorcontrib><creatorcontrib>Citterio, A.</creatorcontrib><creatorcontrib>Di Michele, A.</creatorcontrib><creatorcontrib>Bianchi, C.L.</creatorcontrib><creatorcontrib>Prati, L.</creatorcontrib><creatorcontrib>Pirola, C.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Environment Abstracts</collection><jtitle>Applied catalysis. B, Environmental</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Capelli, S.</au><au>Rosengart, A.</au><au>Villa, A.</au><au>Citterio, A.</au><au>Di Michele, A.</au><au>Bianchi, C.L.</au><au>Prati, L.</au><au>Pirola, C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Bio-adipic acid production by catalysed hydrogenation of muconic acid in mild operating conditions</atitle><jtitle>Applied catalysis. B, Environmental</jtitle><date>2017-12-05</date><risdate>2017</risdate><volume>218</volume><spage>220</spage><epage>229</epage><pages>220-229</pages><issn>0926-3373</issn><eissn>1873-3883</eissn><abstract>[Display omitted]
•Muconic to adipic acid hydrogenation on 5% Pt/C.•Mild conditions: 4bar, 50–70°C, 60–90min.•Catalyst is stable and reusable, 100% selective.•Catalyst characterization pre-post reaction.•Insight on industrial bioprocess downstream.
In this work trans,trans-muconic acid was hydrogenated to adipic acid, a strategic intermediate for the industry of polyamides and high performance polymers. This study: (1) develops a new and robust analytical method for the evaluation of muconic acid conversion and adipic acid selectivity, (2) defines a standard procedure for the confirmation of the kinetic regime using experimental data and some practical criteria to exclude mass transfer limitations, (3) tests Pt/C 5% commercial catalyst for the study of muconic acid hydrogenation at different operating conditions, (4) hypothesizes a reaction pathway in aqueous media, and (5) demonstrates the possibility to recycle the catalyst without loss in activity and selectivity. The developed analytical method evaluates muconic acid conversion by UV–vis analyses, while the selectivity towards adipic acid and mono-unsatured intermediates was determined by GC/TCD analysis after derivatization of the reaction mixture. Under optimized conditions the hydrogenation reaction (70°C, 4bar of hydrogen and 10 substrate/catalyst ratio (wt/wt)) reached full conversion with full selectivity toward adipic acid in 2h. Finally, recycling tests revealed the possibility to reuse catalyst up to 10 times without loss in conversion and selectivity opening the way to a scaling up of the process.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/j.apcatb.2017.06.060</doi><tpages>10</tpages></addata></record> |
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subjects | Acid production Adipic acid Bio-adipic acid Catalysis Catalysts Conversion Heterogeneous catalysis Hydrogen storage Hydrogenation Intermediates Mass transfer Muconic acid Platinum Polyamide resins Polyamides Polymers Scaling Selectivity |
title | Bio-adipic acid production by catalysed hydrogenation of muconic acid in mild operating conditions |
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